Process for the manufacture of alkyl ketene dimer

A process for making an alkyl ketene dimer by the dehydrohalogenation reaction of a C.sub.8 -C.sub.32 aliphatic fatty acid halide with a tertiary amine in a solvent wherein the tertiary amine hydrohalide is mechanically separated from the alkyl ketene dimer solvent solution and wherein the solvent comprises an oxygenated hydrocarbon solvent having a boiling point above 70.degree. C. and Hansen polar and hydrogen bonding solubility values lying on or within the segment of a solubility parameter circle drawn on a parameter solubility map where the x-y axes are the Hansen polar and hydrogen bonding solubility parameter scales in MPa.sup.1/2 units, respectively, the circle radius being 3.5 MPa.sup.1/2, and the center of the circle having 6 and 4 as its x, y coordinates, the Hansen polar and hydrogen bonding solubility values of the oxygenated hydrocarbon solvents having x, y coordinates such that x.sup.2 =y.sup.2 -12x-8y+52.ltoreq.12.25, provided that the Hansen polar solubility value of the oxygenated hydrocarbon solvent is greater than 2.75 MPa.sup.1/2.

A process for making an alkyl ketene dimer by the dehydrohalogenation reaction of a C.sub.8 -C.sub.32 aliphatic fatty acid chloride with a tertiary amine in an inert solvent, the solvent comprising at least 30% of an oxygenated hydrocarbon or mixture of oxygenated hydrocarbons selected from the group consisting of esters other than ethyl acetate, ketones and aromatic ethers.

A process for making an alkyl ketene dimer by the dehydrohalogenation reaction of a C.sub.8 -C.sub.32 aliphatic fatty acid halide with a tertiary amine in a solvent comprising an oxygenated hydrocarbon solvent having a boiling point above 70.degree. C. and wherein the Hansen polar solubility parameter is 6-7 MPa.sup.1/2 and the Hansen hydrogen bonding parameter is 3.5-5.5 MPa.sup.1/2 or the Hansen polar solubility parameter is 3.5-5.5 MPa.sup.1/2 and the Hansen bonding parameter is 6-7 MPa.sup.1/2.

A process for the synthesis of an alkyl ketene dimer by the dehydrohalogenation reaction of a C.sub.8 -C.sub.32 aliphatic fatty acid halide with a tertiary amine in a solvent comprising an oxygenated hydrocarbon solvent selected from the group consisting of ketones, esters other than ethyl acetate, and ethers having a boiling point above 70.degree. C. and, Hansen polar and hydrogen bonding solubility values lying on or within a solubility parameter circle drawn on a parameter solubility map where the x-y axes are the Hansen polar and hydrogen bonding solubility parameter scales in MPa.sup.1/2 units, respectively, the circle radius being 3.5 MPa.sup.1/2, and the center of the circle the center having 6.25 and 4 as its x, y coordinates, the oxygenated hydrocarbon solvent having x, y coordinates such that x.sup.2 +y.sup.2 -12.5x-8y+55.0625.ltoreq.12.25.

A process for making an alkyl ketene dimer by the dehydrohalogenation reaction of a c.sub.8 -C.sub.32 aliphatic fatty acid halide with a tertiary amine in a solvent comprising an oxygenated hydrocarbon solvent selected from the group consisting of ketones, esters other than ethyl acetate, and ethers having a boiling point above 70.degree. C. and Hansen polar and hydrogen bonding solubility values lying on or within the segment of a solubility parameter circle drawn on a parameter solubility map where the x-y axes are the Hansen polar and hydrogen bonding solubility parameter scales in MPa.sup.1/2 units, respectively, the circle radius being 3.5 MPa.sup.1/2, and the center of the circle having 6 and 4 as its x, y coordinates, the Hansen polar and hydrogen bonding solubility values of the oxygenated hydrocarbon solvents having x, y coordinates such that x.sup.2 +y.sup.2 -12x-8y+52.ltoreq.12.25, provided that the Hansen polar solubility value of the oxygenated hydrocarbon solvent is greater than 2.75 MPa.sup.1/2.